Methanesulfonyl chloride → 1-((Methylsulfonyloxy)methyl)cyclopropyl benzoate

HRID 1517907Notes

Reaction equation

HRID 1517907 reaction equation
[C:1]([O:9][C:10]1([CH2:13][OH:14])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[C:1]([O:9][C:10]1([CH2:13][O:14][S:16]([CH3:15])(=[O:18])=[O:17])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 666698541-(Hydroxymethyl)cyclopropyl benzoate

Product 1

HCID 866456091-((Methylsulfonyloxy)methyl)cyclopropyl benzoateYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-(hydroxymethyl)cyclopropyl benzoate (500 mg, 2.6 mmol) and TEA (394 mg, 3.9 mmol, Shantou Xilong chemical factory) in 50 mL of dry CH2Cl2, was added MsCl (357 mg, 3.12 mmol, Shanghai Haiqu chemical Ltd.) dropwise via a syringe at rt. After stirring for 2 hrs at rt, the mixture was diluted with icewater and extracted with CH2Cl2 (30 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give the title compound as pale yellow solid (590 mg, 84%).

Workup

  1. additionthe mixture was diluted with icewater
  2. extractionextracted with CH2Cl2 (30 mL×2)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-218d75a854854b3fa8a4138894623787
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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